Toluene → 4'-Cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester

Participants

Reaction Steps

Procedure I′: 1.8 g of (4-bromophenyl)cyclopropylmethane (8.0 mmol), 1.80 g of (4-methoxycarbonylphenyl)boronic acid (10.0 mmol) are put into flask with 8.0 ml of aqueous 2M K2CO3 and 90 ml of toluene:EtOH=20:1. The mixture is deoxygenated and stirred at room temperature under N2 for 30 min. 280 mg of tetrakis(triphenylphosphine)-palladium is added. The reaction mixture is stirred under reflux for overnight. Organic layer is separated from water layer and water layer is extracted with CH2Cl2. All organic layers are combined together and dried over Na2SO4 and evaporated. The crude product is applied to silica-gel column chromatography (Hexane:AcOEt=8:1→3:1). 4′-Cyclopropanecarbonyl-biphenyl-4-carboxylic acid methyl ester is recrystallized from hexane/AcOEt (849 mg, 38%). Mass spectrum (m/e): 214 (M+1)

Provenance & Evidence